Hydrochloric Acid → HCID 19880358, compound

HRID 1885235Notes

Reaction equation

HRID 1885235 reaction equation
[BH4-].[Na+].[OH:3][C:4]([CH3:34])([CH2:21][CH2:22][C:23]1[C:24](=[O:33])[C:25]([CH3:32])=[C:26]([CH3:31])[C:27](=[O:30])[C:28]=1[CH3:29])[CH2:5][O:6][C:7]1[CH:20]=[CH:19][C:10]([CH2:11][CH:12]2[S:16][C:15](=[O:17])[NH:14][C:13]2=[O:18])=[CH:9][CH:8]=1.Cl>C(O)C>[OH:33][C:24]1[C:25]([CH3:32])=[C:26]([CH3:31])[C:27]([OH:30])=[C:28]([CH3:29])[C:23]=1[CH2:22][CH2:21][C:4]([OH:3])([CH3:34])[CH2:5][O:6][C:7]1[CH:20]=[CH:19][C:10]([CH2:11][CH:12]2[S:16][C:15](=[O:17])[NH:14][C:13]2=[O:18])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 9911974HCID 9911974, compound

Product 1

HCID 19880358HCID 19880358, compoundYield 89.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

165 mg of sodium borohydride were added, whilst ice-cooling and stirring, to a solution of 1 g of 5-{4-[2-hydroxy-2-methyl-4-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)butoxy]benzyl}-2,4-dioxothiazolidine (prepared as described in Example 1) dissolved in 10 ml of ethanol, and the resulting mixture was stirred at room temperature for 30 minutes. At the end of this time, the reaction mixture was poured into a mixture of 100 ml of ice-water and 0.6 ml of 35% v/v aqueous hydrochloric acid to precipitate white crystals. The crystals were collected by filtration and dried in vacuo over phosphorous pentoxide to afford 0.9 g of the title compound as a yellow powder melting at 84°-88° C.

Workup

  1. temperaturecooling
  2. customto precipitate white crystals
  3. filtrationThe crystals were collected by filtration
  4. dry with materialdried in vacuo over phosphorous pentoxide

Sources & evidence

ORD record
ord-9d7935c2f2004d729013991dc62ca74c
Source dataset
uspto-grants-1992_09
Patent number
US05143930

Reaction notes

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